2-溴萘 | 580-13-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-溴萘
• 中文别名: Β-溴代萘；2-溴化萘；2-溴代萘；β-溴萘；β-溴代萘
• 英文名称: 2-bromonaphthalene
• 英文别名: 2-bromonaphtalene；2-bromonapthalene；2-naphthyl bromide；β-bromo-naphthalene
• CAS: 580-13-2
• 化学式: C₁₀H₇Br
• mdl: MFCD00004051
• 分子量: 207.07
• InChiKey: APSMUYYLXZULMS-UHFFFAOYSA-N

物化性质

• 熔点：
  52-55 °C (lit.)
• 沸点：
  281-282 °C (lit.)
• 密度：
  1,605 g/cm3
• 闪点：
  >230 °F
• 溶解度：
  溶于甲醇：50mg/mL，澄清，无色至黄色

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• WGK Germany：
  3
• 海关编码：
  29036990
• 安全说明：
  S26,S36,S36/37,S45
• 危险品运输编号：
  UN 1230 3/PG 2
• 危险品标志：
  Xn
• 危险类别码：
  R22,R36
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  本品应密封避光保存。

SDS

Name:	2-Bromonaphtalene 99% (GC) Material Safety Data Sheet
Synonym:	Tert-Butyl Bromid
CAS:	580-13-2

Section 1 - Chemical Product MSDS Name:2-Bromonaphtalene 99% (GC) Material Safety Data Sheet
Synonym:Tert-Butyl Bromid

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
580-13-2	2-Bromonaphthalene	99 (GC)	209-452-5

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

---

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 gastrointestinal irritation with nausea, vomiting and diarrhea. 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.

---

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 immediately.
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 immediately. 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:

---

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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. 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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 580-13-2: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 281 - 282 deg C
Freezing/Melting Point: 52 - 55 deg C
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water: slightly soluble in water
Specific Gravity/Density:
Molecular Formula: C10H7Br
Molecular Weight: 207.07

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases, bromine fumes, bromine.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 580-13-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromonaphthalene - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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# 580-13-2: No information available.
Canada
CAS# 580-13-2 is listed on Canada's NDSL List.
CAS# 580-13-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 580-13-2 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

理化性质

2-溴萘又名β-溴萘，为白色或黄色片状结晶。其分子量为207.07，熔点59℃，沸点在281～282℃之间，相对密度为1.605（0/4℃），折射率为1.6382（60℃）。该物质溶于苯、醚、氯仿和二硫化碳，微溶于水。有毒性，其毒性与氯萘相近，主要用于制备染料。

合成

2-溴萘可通过2-萘胺的桑德迈尔反应获得。首先将2-萘胺进行重氮化处理，再用溴化亚铜处理即可得到产物。

化学性质

2-溴萘为无色晶体，不溶于水，但可溶于乙醇、乙醚和苯中。它与1-溴萘是同分异构体。

用途

主要用作医药中间体及有机合成和染料中间体。

生产方法

由2-萘酚与溴反应制备：

1. 将0.55摩尔三苯基磷和125毫升乙腈混合，在冰浴中冷却，搅拌下滴加88克溴，并保持反应温度在40℃以下。
2. 撤去冰浴后，加入0.5摩尔2-萘酚和100毫升乙腈的混合液，并于60～70℃加热超过0.5小时。
3. 蒸出乙腈，升高温度直至所有固体熔化。继续升温至340℃，直至不再有溴化氢放出。
4. 反应物冷却至约100℃，倒入烧杯中并冷至室温。加入300毫升庚烷或石油醚使固体成细沉淀，过滤，并用300毫升戊烷洗涤两次。
5. 合并滤液及戊烷萃取液，用200毫升20%氢氧化钠清洗后，再用无水硫酸镁干燥。最后通过状态蒸馏可得2-溴萘72～81克，产率为70%~80%。

反应信息

• 作为反应物：
  描述：

  2-溴萘 在 正丁基锂 、 [RhCl(cyclooctene)2]2 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 生成 2-甲基萘
  参考文献：
  名称：

  炔烃、氯化芳基锌和碘甲烷的铑催化三组分反应产生有/无 1,4-迁移的三取代/四取代烯烃

  摘要：

  发现在铑催化剂存在下进行炔烃、芳基氯化锌和碘甲烷的三组分反应，以产生高产率的三取代/四取代烯烃。通常的芳基氯化锌仅产生三取代的烯烃，通过迁移的碳化 - 交叉偶联序列产生，其中 1,4-Rh 从烯基碳迁移到芳基碳。相比之下，5 元杂芳基氯化锌仅通过碳化-交叉偶联途径产生四取代烯烃，而没有 1,4-迁移。

  DOI：

  10.1021/acs.orglett.2c02299
• 作为产物：
  描述：

  2-萘三氟硼酸钾 在 tetra-N-butylammonium tribromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以99%的产率得到2-溴萘
  参考文献：
  名称：

  使用三溴化四丁基铵或三碘化铯对有机三氟硼酸盐进行卤代硼烷化

  摘要：

  报道了在水介质中使用市售的三溴化四丁基铵（TBATB）或三碘化铯对有机三氟硼酸盐进行卤代硼烷化。事实证明，这种温和的不含过渡金属的方法可耐受多种官能团。观察到高的区域选择性和化学选择性。两个合成路线（ż）从炔-dibromoalkenes，通过stereodefined（ż）-2- bromoalkenyltrifluoroborates和（Ž）-1,2-双（硼烷基）alkenyltrifluoroborates，已经使用TBATB介导bromodeboronation作为关键步骤开发的。

  DOI：

  10.1016/j.tet.2012.03.016
• 作为试剂：
  描述：

  7-氮杂吲哚 在 2-溴萘 、 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 、 氩 为溶剂， 反应 24.0h， 以44%的产率得到1-(naphthalen-2-yl)-1H-indole
  参考文献：
  名称：

  Substituted pyrroline kinase inhibitors

  摘要：

  本发明涉及新型取代吡咯烯化合物，可用作激酶抑制剂，并用于治疗或改善激酶介导的疾病的方法。

  公开号：

  US20040006095A1

文献信息

• Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides
  作者：Zhong Lian、Hongfei Yin、Stig D. Friis、Troels Skrydstrup

  DOI：10.1039/c5cc02085a

  日期：——

  This first carbonylative coupling employing a phosphorus-based nucleophile provides easy and safe access to acyl phosphonates under mild conditions.

  这种首次使用磷基亲核试剂的羰基化偶联反应在温和条件下提供了对酰基膦酸酯的简便安全访问。
• Synthese und flüssigkristalline Eigenschaften 2,6-disubstituierter Naphthaline
  作者：Urs H. Lauk、Peter Skrabal、Heinrich Zollinger

  DOI：10.1002/hlca.19850680533

  日期：1985.8.14

  Synthesis and Liquid-Crystal Properties of 2,6-Disubstituted Naphthalene Derivatives

  2,6-二取代萘衍生物的合成及液晶性能
• Substituted imidazol-pyridazine derivatives
  申请人：——

  公开号：US20030229096A1

  公开（公告）日：2003-12-11

  The present invention relates to compounds of formula 1 wherein A is an unsubstituted or substituted cyclic group; and R is hydrogen or lower alkyl; or a pharmaceutically acceptable acid addition salt thereof. These compounds are NMDA NR-2B receptor subtype specific blockers and are useful in the treatment of neurodegeneration, depression and pain.

  本发明涉及以下式的化合物 1 其中A是未取代或取代的环状基团；以及 R是氢或较低的烷基； 或其药学上可接受的酸盐。这些化合物是NMDA NR-2B受体亚型特异性阻断剂，对于治疗神经退行性疾病、抑郁症和疼痛具有用处。
• Fungicides for the control of take-all disease of plants
  申请人：Monsanto Company

  公开号：US05498630A1

  公开（公告）日：1996-03-12

  A method of controlling Take-All disease of plants by applying a fungicide of the formula ##STR1## wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; and A is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR.sub.3, --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ; B is --W.sub.m --Q(R.sub.2).sub.3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ; Q is C, Si, Ge, or Sn; W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W is selected from --C(R.sub.3).sub.p H(.sub.2-p), --N(R.sub.3).sub.m H(.sub.1-m)--, --S(O)p--, and --O--; X is 0 or S; n is 0, 1, 2, or 3; m is 0 or 1; p is 0, 1, or 2; each R and R.sub.2 is independently defined herein; R.sub.3 is C.sub.1 -C.sub.4 alkyl; R.sub.4 is C.sub.1 -C.sub.4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R.sub.7 is C.sub.1 -C.sub.4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R.sub.4 ; or an agronomic salt thereof.

  一种通过施用公式##STR1##的杀菌剂来控制植物全蚀病的方法，其中Z1和Z2为C，并且是苯并噻吩的芳香环的一部分；A从--C(X)-胺中选择，其中胺是未取代的、单取代的或双取代的氨基基团，--C(O)--SR.sub.3，--NH--C(X)R.sub.4和--C(.dbd.NR.sub.3)--XR.sub.7；B为--W.sub.m --Q(R.sub.2).sub.3或从O-甲苯基、1-萘基、2-萘基和9-菲基中选择，每个都可以选择性地用卤素或R.sub.4取代；Q为C、Si、Ge或Sn；W为--C(R.sub.3).sub.p H.sub.(2-p)--；或当Q为C时，W从--C(R.sub.3).sub.p H(.sub.2-p)，--N(R.sub.3).sub.m H(.sub.1-m)--，--S(O)p--和--O--中选择；X为0或S；n为0、1、2或3；m为0或1；p为0、1或2；每个R和R.sub.2在此独立定义；R.sub.3为C.sub.1 -C.sub.4烷基；R.sub.4为C.sub.1 -C.sub.4烷基、卤代烷基、烷氧基、烷硫基、烷基氨基或二烷基氨基；R.sub.7为C.sub.1 -C.sub.4烷基、卤代烷基或苯基，可以选择性地用卤素、硝基或R.sub.4取代；或其农艺学盐。
• Highly Diastereoselective Crown Ether Catalyzed Arylogous Michael Reaction of 3-Aryl Phthalides
  作者：Marina Sicignano、Antonella Dentoni Litta、Rosaria Schettini、Francesco De Riccardis、Giovanni Pierri、Consiglia Tedesco、Irene Izzo、Giorgio Della Sala

  DOI：10.1021/acs.orglett.7b02113

  日期：2017.8.18

  The first arylogous Michael reaction of 3-aryl phthalides has been developed. The reaction, promoted by catalytic amounts of KOH or K3PO4 and dibenzo-18-crown-6, affords the corresponding 3,3-disubstituted phthalides in good to high yields and as single diastereomers in nearly all studied cases.

  已经开发了第一个3-芳基邻苯二甲酸酯的迈克尔反应。由催化量的KOH或K 3 PO 4和二苯并18-冠-6促进的反应，以几乎所有的研究情况，均以高收率和高收率提供了相应的3,3-二取代邻苯二甲酸酯。

表征谱图