β-苯丙醛二甲缩醛 | 90-87-9

• 物质功能分类: 香精与香料 - 合成香料 - 缩羰基类香料
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: β-苯丙醛二甲缩醛
• 中文别名: (2,2-二甲氧基-1-甲基乙基)苯；2-苯基-1-丙醛缩二甲醇；龙葵醛缩二甲醇；龙葵醛二甲醇缩醛
• 英文名称: 2-phenylpropionaldehyde dimethyl acetal
• 英文别名: 1,1-dimethoxypropan-2-ylbenzene
• CAS: 90-87-9
• 化学式: C₁₁H₁₆O₂
• mdl: MFCD00008860
• 分子量: 180.247
• InChiKey: UFOUDYPOSJJEDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  100-101 °C12 mm Hg(lit.)
• 密度：
  0.992 g/mL at 25 °C(lit.)
• 闪点：
  198 °F
• 溶解度：
  Almost insoluble in water, soluble in alcohol oils.
• LogP：
  3 at 25℃
• 物理描述：
  Colourless to slightly yellow liquid; Strong, warm, spicy aroma reminiscent of walnut
• 折光率：
  1.492-1.497

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• RTECS号：
  MU6480000

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Phenylpropionaldehyde dimethyl acetal
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 90-87-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 1,1-Dimethoxy-2-phenylpropane
Hydratropic aldehyde dimethyl acetal
Formula : C11H16O2
Molecular Weight : 180,24 g/mol
CAS-No. : 90-87-9
EC-No. : 202-022-8
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Phenylpropionaldehyde-dimethyl acetal
CAS-No. 90-87-9 Acute Tox. 4; Skin Irrit. 2; Eye <= 100 %
EC-No. 202-022-8 Irrit. 2; STOT SE 3; H302,
H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Phenylpropionaldehyde-dimethyl acetal
CAS-No. 90-87-9 Xi, R36/37/38 <= 100 %
EC-No. 202-022-8
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13). Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 100 - 101 °C at 16 hPa - lit.
boiling range
g) Flash point 92 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,992 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agents, Strong acids
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 1.850 mg/kg
Inhalation: no data available
LD50 Dermal - rabbit - > 5.000 mg/kg
Skin corrosion/irritation
Skin - rabbit
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: MU6480000
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Eye Irrit. Eye irritation
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
Full text of R-phrases referred to under sections 2 and 3
Xi Irritant
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

含量分析

按乙缩醛测定法（OT-2）测定。取样量为2g，计算中的当量因子(e)取90.13。

或可采用气相色谱法（GT-10-4），使用非极性柱进行测定。

毒性

GRAS（FEMA）认证。

使用限量

FEMA（mg/kg）：
软饮料 - 0.26
冷饮 - 0.51
糖果 - 1.5
焙烤食品 - 31
胶姆糖 - 5.0
调味品 - 5.0

适度为限（FDA §172．515，2000）。

化学性质

无色至微黄色液体，具有类似蘑菇的香气。溶于乙醇和乙醚，几乎不溶于水。沸点241℃。

用途

主要用于香料，特别适用于配制蘑菇、香辛料、坚果等类型的香精。

生产方法

在胶体钯存在下，由二甲基乙缩醛催化氢化而成。也可通过2-苯丙醛和盐酸的甲醇溶液来制备。

反应信息

• 作为反应物：
  描述：

  β-苯丙醛二甲缩醛 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 2-苯基丙醛
  参考文献：
  名称：

  一种简单有效的使用三氟甲磺酸铋催化缩醛和缩酮的化学选择性方法。

  摘要：

  三氟甲基磺酸铋是一种高效的催化剂（0.1-1 mol％），用于缩醛和缩酮的脱保护。该方法非常简便，对衍生自酮和共轭醛的缩醛具有选择性。叔丁基二甲基甲硅烷基醚对反应条件稳定。三氟甲磺酸铋的高度催化性质和相对无毒的溶剂系统（THF / H（2）O）的使用使该程序特别适合大规模合成。

  DOI：

  10.1021/jo016180s
• 作为产物：
  描述：

  (4-benzenesulfonyl-1-methyl-4-nitrobut-2-enyl)benzene 在 magnesium sulfate 、 对甲苯磺酸 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 β-苯丙醛二甲缩醛
  参考文献：
  名称：

  脂族醛的双向同系化：通过相同的中间体进行一碳的缩短和延长

  摘要：

  脂肪醛可通过相同的中间体β，γ-不饱和α-硝基砜，经脯氨酸催化的连续反应制备的相同中间体，通过2–4个反应，与一碳短和一碳长的同源羰基化合物同源。几种脂肪醛与苯磺酰基硝基甲烷。当关键中间体的氧化裂解得到一碳较少的同源羰基化合物时，相同关键中间体的还原随后被氧化产生了更多一碳的同源羰基化合物。

  DOI：

  10.1016/j.tet.2019.130883

文献信息

• Reaction of α,β-unsaturated and α-phenyl acetals with epoxides, promoted by lithium. Potassium mixed base LICKOR: Synthesis of homoallyl alcohols
  作者：Annamaria Deagostino、Cristina Prandi、Paolo Venturello

  DOI：10.1016/0040-4020(95)00969-8

  日期：1996.1

  Acetals 1, 7 and 8, in the presence of the mixed metal base LICKOR, undergo deprotonation and elimination reactions, affording enol ethers intermediates. Further hydrogen-metal exchange at the α-vinyl site of elimination products gives α-metalated species that yield, by reaction with epoxides, homoallyl alcohols. Experimental procedures are given for the conversion of the unsaturated species into the

  缩醛1，7和8，在混合金属基底LICKOR的存在下，进行脱质子化和消除反应，得到烯醇醚中间体。在消除产物的α-乙烯基位点进一步进行氢-金属交换，得到α-金属化的物种，该物种通过与环氧化物反应生成均烯丙基醇。给出了将不饱和物质转化为相应的羰基化合物的实验程序。α-取代的乙氧基二烯4也是一锅合成2,6-二取代的四氢-4 H-吡喃-4-酮19的有用中间体。
• Methoxychlorination and dimethoxylation of alkenes the reactions of substituted styrenes with phenylselenenyl chloride in methanol
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Donatella Chianelli、Donatella Bartoli

  DOI：10.1016/s0040-4020(01)81734-8

  日期：1988.1

  addition of PhSeCl to α- and β-substituted styrenes in methanol is regio- and stereospecific and affords the products of methoxyselenenylation. These compounds further react with PhSeCl to give the deselenenylation products. In the case of α-substituted styrenes, 1-methoxy, 2-chloroalkanes are produced, whereas with β-substituted styrenes the major reaction products are the 1,2-dimethoxyalkanes and

  在甲醇中向α-和β-取代的苯乙烯中添加PhSeCl具有区域和立体特异性，并提供甲氧基硒烯化的产物。这些化合物进一步与PhSeCl反应，得到去硒烯基化产物。在α-取代的苯乙烯的情况下，产生了1-甲氧基，2-氯代烷烃，而对于β-取代的苯乙烯，主要的反应产物是发生苯基迁移的1,2-二甲氧基烷烃和2,2-二甲氧基烷烃。结果表明，这些反应是通过中间形成烷基苯基氯化二苯酚PhCR（OMe）CHR 1 SeCl 2 Ph来进行的，而中间反应机理取决于起始烯烃的结构。
• Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals
  作者：Swamy Peraka、Naresh Mameda、Mahender Reddy Marri、Srujana Kodumuri、Durgaiah Chevella、Prabhakar Sripadi、Narender Nama

  DOI：10.1039/c5ra16826k

  日期：——

  salt and oxone is reported. The preliminary mechanistic investigations suggest that the key factor for achieving the anti-Markovnikov regioselectivity is the semipinacol rearrangement of an iodo functionalized intermediate, which is confirmed by an isotope labeling experiment. In addition, the reaction involves the de-iodination of a co-iodo intermediate via its oxidation to hypervalent iodine species

  报道了一种新的无金属的，乙烯基芳烃的催化双甲氧基化的乙烯基芳烃，其基于从碘化物盐和氧酮原位生成的HOI物质。初步的机理研究表明，实现抗马尔科夫尼科夫区域选择性的关键因素是碘官能化中间体的频哪醇重排，这通过同位素标记实验得以证实。此外，该反应涉及的去碘化共碘中间经由氧化成高价碘，而不是由亲电试剂将其抽象为碘化物。HRESI-MS研究支持在芳族烯烃催化转化为相应的缩醛的过程中，将含一价碘的中间体转化为三价碘的中间体。
• A generalized approach for iron catalyzed chemo- and regioselective formation of anti-Markovnikov acetals from styrene derivatives
  作者：Abhishek Dutta Chowdhury、Goutam Kumar Lahiri

  DOI：10.1039/c2cc17889c

  日期：——

  in the presence of pyridine-2,6-dicarboxylic acid and PhI(OAc)(2) can efficiently catalyze the formation of chemoselective dialkyl acetals from styrene derivatives with anti-Markovnikov regioselectivity in good to high yields under mild and benign reaction conditions.

  在吡啶2,6-二羧酸和PhI（OAc）（2）存在下的Fe（BF（4））（2）.6H（2）O可以有效地催化苯乙烯衍生物与抗氧化剂形成化学选择性二烷基乙缩醛-Markovnikov区域选择性在温和和良性反应条件下具有良好至高收率。
• A NOVEL AND USEFUL METHOD FOR THE PREPARATION OF METHYL ESTERS FROM DIMETHYL ACETALS
  作者：Teruaki Mukaiyama、Jun-ichi Kato、Norikazu Miyoshi、Nobuharu Iwasawa

  DOI：10.1246/cl.1985.1255

  日期：1985.8.5

  In the presence of a catalytic amount of trityl perchlorate, acetal-type peroxides are successfully prepared from dimethyl acetals and t-butyl trimethylsilyl peroxide in good yields. The peroxides thus obtained are converted to the corresponding methyl esters also in good yields.

  在催化量的高氯酸三苯甲基存在下，由二甲基缩醛和叔丁基三甲基甲硅烷基过氧化物以良好的收率成功制备了缩醛型过氧化物。如此获得的过氧化物也以良好的产率转化为相应的甲酯。

表征谱图