1,3-二溴丙酮 | 816-39-7

• 物质功能分类: 香精与香料 - 合成香料 - 酮类香料
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,3-二溴丙酮
• 中文别名: 1,3-二溴-2-丙酮；1,3-二溴乙酮
• 英文名称: 1,3-dibromoroacetone
• 英文别名: 1,3-Dibromoacetone；1,3-dibromopropan-2-one
• CAS: 816-39-7
• 化学式: C₃H₄Br₂O
• 分子量: 215.872
• InChiKey: LQQKDSXCDXHLLF-UHFFFAOYSA-N

物化性质

• 熔点：
  29-30℃
• 沸点：
  95 °C (20 mmHg)
• 密度：
  2.12
• 闪点：
  97-98°C/21mm
• 溶解度：
  易溶于丙酮、氯仿、二氯甲烷和甲醇。
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与酸和氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  8
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090
• 危险品运输编号：
  2927
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	1 3-Dibromo-2-Propanone Material Safety Data Sheet
Synonym:	None
CAS:	816-39-7

Section 1 - Chemical Product MSDS Name:1 3-Dibromo-2-Propanone Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
816-39-7	2-Propanone, 1,3-Dibromo-	ca 100	212-430-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Avoid runoff into storm sewers and ditches which lead to waterways.
Clean up spills immediately, observing precautions in the Protective Equipment section. Absorb spill using an absorbent, non-combustible material such as earth, sand, or vermiculite. Do not use combustible materials such as sawdust. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 816-39-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear almost colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 95 deg C @ 20.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C3H4Br2O
Molecular Weight: 215.87

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen bromide, bromine fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 816-39-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Propanone, 1,3-Dibromo- - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 816-39-7: No information available.
Canada
CAS# 816-39-7 is listed on Canada's NDSL List.
CAS# 816-39-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 816-39-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生产方法

1,3-二溴丙酮的合成主要有两种方法：丙酮法和丙三醇法。

（1）通过丙酮直接溴化制备1,3-二溴丙酮。具体步骤如下： 在2L烧瓶中，加入99.0g（1.71mol）丙酮、98.2g（1.64mol）乙酸和400g水；搅拌下，通过滴液漏斗分批加入475g（2.97mol）溴，并调节漏斗中的压力以控制溴的滴加速度。反应温度维持在60℃，大约需要10小时完成加料过程。冷却混合物至室温后，静置48小时并分离下层液体；然后用MgSO₄干燥，再进行减压蒸馏，最终得到97.6g（30.4%）的1,3-二溴丙酮。应注意处理水层时要格外小心，因为其中含有HBr。

（2）由丙三醇经溴化和氧化制备1,3-二溴丙酮的过程如下： 将1000g（10.8mol）丙三醇、25g（1.0mol）红磷和1869g（23.4mol）溴加入烧瓶中，反应后可获得1,3-二溴丙醇，产率为59%。随后加入重铬酸钾和硫酸进行氧化反应，以得到1,3-二溴丙酮，其产率可达67%。此方法的主要优点是生成的异构体较少，而直接用丙酮溴化时不可避免地会遇到生成异构体的问题。

反应信息

• 作为反应物：
  描述：

  1,3-二溴丙酮 在 potassium chloride 作用下， 以 水 为溶剂， 反应 0.33h， 以98%的产率得到1,3-二氯丙酮
  参考文献：
  名称：

  [EN] PROCESS FOR PREPARIING 1,3-DIBROMOACETONE, 1-3-DICHLOROACETONE AND EPICHLOROHYDRIN
  [FR] PROCEDE DE PREPARATION DE 1,3-DIBROMOACETONE, 1,3-DICHLOROACETONE ET EPICHLOROHYDRINE

  摘要：

  公开号：

  WO2005115954A3
• 作为产物：
  描述：

  1,3-二溴-2-丙醇 在 高碘酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到1,3-二溴丙酮
  参考文献：
  名称：

  使用均相和非均相介质快速合成甘油1,3-二氯醇中的1,3-二羟基丙酮，1,3-二氯，1,3-二溴和1,3-二碘丙酮

  摘要：

  从甘油1,3-二氯醇生产1,3-二羟基丙酮（1），1,3-二氯丙酮（6），1,3-二溴丙酮（7）和1,3-二碘丙酮（8）的新的高效繁殖途径（3）开发。从甘油2（1,3-选择性氯化2至3，氧化3至6和随后的二羟基化）三个步骤处理1的合成，总收率为51％。另一方面，分别通过反式溴化和反式碘化从3生成7和8，然后进行氧化和羟基化步骤，总产率为38-52％。它使用了带有不同试剂（HCl / AcOH，氯铬酸吡啶鎓（PCC），PCC-HIO4）的均相介质，以及负载在聚合物树脂上的试剂（例如Amberlyst A26-HCrO形式）的均质介质，

  DOI：

  10.21577/0103-5053.20200058

文献信息

• NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME
  申请人：Ryono Denis E.

  公开号：US20080009465A1

  公开（公告）日：2008-01-10

  Compounds are provided which are phosphonate and phosphinate activators and thus are useful in treating diabetes and related diseases and have the structure wherein is a heteroaryl ring; R 4 is —(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 ), —(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g , —(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g , —(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10 ), or —(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10 ); R 5 and R 6 are independently selected from H, alkyl and halogen; Y is R 7 (CH 2 ) s or is absent; and X, n, Z, m, R 4 , R 5 , R 6 , R 7 , and s are as defined herein; or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.

  提供了磷酸酯和磷酸酯激活剂，因此在治疗糖尿病和相关疾病方面非常有用，并具有以下结构： 其中 是杂环芳基环； R 4 为—(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 )、—(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g 、—(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g 、—(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10) 或—(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10) ； R 5 和R 6 分别选择自H、烷基和卤素； Y为R 7 (CH 2 ) s 或不存在；以及 X、n、Z、m、R 4 、R 5 、R 6 、R 7 和s如本文所定义；或其药用盐。 还提供了一种利用上述化合物治疗糖尿病和相关疾病的方法。
• [EN] NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME<br/>[FR] NOUVEAUX ACTIVATEURS DE LA GLUCOKINASE ET MÉTHODES D'UTILISATION DESDITS ACTIVATEURS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011130459A1

  公开（公告）日：2011-10-20

  Compounds are provided which are activators of the enzyme glucokinase and thus are useful in treating diabetes and related diseases, which compounds have the structure wherein R1, R2, R3, R4, R5, R6, Y and X are as defined herein or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related disease employing the above compounds is also provided.

  提供了一些化合物，这些化合物是葡萄糖激酶的激活剂，因此在治疗糖尿病和相关疾病方面很有用，这些化合物的结构式中，R1、R2、R3、R4、R5、R6、Y和X如本文所述，或其药用可接受盐。还提供了一种使用上述化合物治疗糖尿病和相关疾病的方法。
• Direct Sulfide-Catalyzed Enantioselective Cyclopropanations of Electron-Deficient Dienes and Bromides
  作者：Qing-Zhu Li、Xiang Zhang、Rong Zeng、Qing-Song Dai、Yue Liu、Xu-Dong Shen、Hai-Jun Leng、Kai-Chuan Yang、Jun-Long Li

  DOI：10.1021/acs.orglett.8b01537

  日期：2018.6.15

  A catalytic highly regioselective, diastereoselective, and enantioselective cyclopropanation of electron-deficient dienes and bromides via direct sulfide organocatalysis is reported. A variety of vinylcyclopropanes featuring a quaternary chiral center were synthesized in up to 99% yield and up to 98:2 enantiomeric ratio (er). These products could be facilely transformed to various interesting molecules

  报道了通过直接硫化物有机催化对缺电子的二烯和溴化物进行高度区域选择性，非对映选择性和对映选择性的环丙烷化反应。以高达99％的收率和高达98：2的对映体比率（er）合成了多种具有季手性中心的乙烯基环丙烷。这些产物可以容易地转化为具有极大结构多样性的各种有趣的分子。
• Reactivity of Various α-Halo Ketones in One-Pot Synthesis of γ-Iminolactones
  作者：Sakineh Asghari、Ahmad Khabbazi Habibi

  DOI：10.1080/00397911.2011.571806

  日期：2012.10

  Abstract The highly reactive 1:1 intermediate generated in the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylate is trapped by α-halo ketones to produce halogenated iminolactones as the sole product in good yields. GRAPHICAL ABSTRACT

  摘要 异氰叔丁酯和乙炔二羧酸二烷基酯反应生成的高反应性 1:1 中间体被 α-卤代酮捕获，以高产率生成卤代亚氨基内酯作为唯一产物。图形概要
• 一类含氮稠环化合物及其制备方法和用途
  申请人：上海凌达生物医药有限公司

  公开号：CN109721600B

  公开（公告）日：2021-04-27

  本发明公开了一类含氮稠环类化合物及其制备方法和用途。本发明的含氮稠环类化合物的结构如下式(I)所示，其中各基团的定义如说明书中所述。本发明的含氮稠环类化合物属于新型的特异性FGFR激酶不可逆抑制剂，可以用于治疗FGFR激酶异常引起的相关疾病如肿瘤。