2,4-二溴-6-甲基苯胺 | 30273-41-7

• 物质功能分类: 有机原料 - 氨基化合物
• 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: 2,4-二溴-6-甲基苯胺
• 中文别名: 6-甲基-2,4-二溴苯胺；4,6-二溴邻甲基苯胺
• 英文名称: 2,4-dibromo-6-methylaniline
• 英文别名: 4,6-dibromo-2-methylaniline；2-Amino-3,5-dibromotoluene
• CAS: 30273-41-7
• 化学式: C₇H₇Br₂N
• mdl: MFCD00735681
• 分子量: 264.947
• InChiKey: LOOOTYOQFFOBCI-UHFFFAOYSA-N

物化性质

• 熔点：
  44-49 °C
• 沸点：
  281.2±35.0 °C(Predicted)
• 密度：
  1.8413 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36/37/39
• 海关编码：
  2921430090
• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22,R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	2 4-Dibromo-6-methylaniline Material Safety Data Sheet
Synonym:	2-Amino-3,5-dibromotoluene4,6-Dibromo-o-toluidin
CAS:	30273-41-7

Section 1 - Chemical Product MSDS Name:2 4-Dibromo-6-methylaniline Material Safety Data Sheet
Synonym:2-Amino-3,5-dibromotoluene4,6-Dibromo-o-toluidin

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
30273-41-7	2,4-Dibromo-6-methylaniline		unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
Not available.

---

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.
Ingestion:
Get medical aid. Wash mouth out with 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 30273-41-7: Personal Protective Equipment Eyes: Not available.
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: Powder
Color: off-white to brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 44-49 deg C
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: C7H7Br2N
Molecular Weight: 264.95

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 30273-41-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,4-Dibromo-6-methylaniline - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 30273-41-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 30273-41-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 30273-41-7 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
针状结晶体，熔点为50℃，可溶于乙醇，并能随蒸汽挥发（也有报道其熔点在39-41℃之间）。

用途
用作医药中间体，主要用于生产新型祛痰剂溴己胺盐酸盐（即必嗽平）。

生产方法
由邻甲苯胺经溴化而制得。将氯仿和邻甲苯胺加入反应锅中，在20-25℃下滴加溴素，约3-4小时滴完后，升温回流10小时。冷却后用氨水调节pH至9-10，静置分层，收集氯仿层并回收氯仿即可得到成品。

反应信息

• 作为反应物：
  描述：

  2,4-二溴-6-甲基苯胺 在 potassium nitrite 、 溶剂黄146 作用下， 以95%的产率得到5,7-二溴-1H-吲唑
  参考文献：
  名称：

  Efficient and Scalable Synthesis of 3,5,7-Trisubstituted 1H-Indazoles as Potent IKK2 Inhibitors

  摘要：

  我们开发了 3,5,7-三取代 1H-吲唑的高效和可扩展的化学方法，并将其应用于 4-[7-（氨基甲酰基）-5-溴-1H-吲唑-3-基]-1-哌啶羧酸 1,1-二甲基乙酯的合成，该化合物是 3,5,7-三取代 1H-吲唑的关键中间体，被鉴定为一种强效 IKK2 抑制剂。该序列可通过八个步骤规模化地制备目标化合物，并能从容易获得的起始原料中以 40% 的总收率进行制备。

  DOI：

  10.1055/s-0028-1087364
• 作为产物：
  描述：

  邻甲苯胺 在 氢溴酸 、 二甲基亚砜 作用下， 反应 2.0h， 以78%的产率得到2,4-二溴-6-甲基苯胺
  参考文献：
  名称：

  在温和条件下用 DMSO/HBr 选择性溴化吡咯衍生物、咔唑和芳香胺

  摘要：

  使用 DMSO/HBr 系统溴化吡咯衍生物、咔唑和芳香胺可提供相应溴化合物的高产率。苯胺溴化中使用的温度控制有助于促进单溴化或二溴化产品的选择性形成。操作简单、毒性低、选择性高，使其成为一种很有前途的芳香族化合物溴化新工艺。

  DOI：

  10.3184/174751914x14114780483352

文献信息

• Halogenation Using Quaternary Ammonium Polyhalides. VI. Bromination of Aromatic Amines by Use of Benzyltrimethylammonium Tribromide
  作者：Shoji Kajigaeshi、Takaaki Kakinami、Kazuhisa Inoue、Manabu Kondo、Hiroko Nakamura、Masahiro Fujikawa、Tsuyoshi Okamoto

  DOI：10.1246/bcsj.61.597

  日期：1988.2

  The reaction of aromatic amines with benzyltrimethylammonium tribromide in dichloromethane–methanol containing calcium carbonate powder for 0.5 h at room temperature gave bromo-substituted aromatic amines in good yields.

  芳香胺与三溴化苄基三甲基铵在含有碳酸钙粉末的二氯甲烷-甲醇中在室温下反应 0.5 小时，以良好的收率得到溴取代的芳香胺。
• [EN] A PROCESS FOR THE SYNTHESIS ANTHRANILIC DIAMIDE COMPOUNDS AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE COMPOSÉS DIAMIDE ANTHRANILIQUE ET INTERMÉDIAIRES ASSOCIÉS
  申请人：PI INDUSTRIES LTD

  公开号：WO2020170178A1

  公开（公告）日：2020-08-27

  The present invention disclosed a process for the synthesis of anthranilic diamide compound of formula (I), wherein, R1, R2, R3a, R3b, R3c, R4, R5, R6 and Z are as defined in the detailed description. The process comprising the step of obtaining a mono- or dicyano substituted aniline compound of formula (IV) which is then converted to an anthranilic acid compound of formula (V) or an anthranilic amide compound of formula (Va). Further, the compound of formula (VI) can be optionally synthesized from compound of formula (IV or V or Va).

  本发明揭示了一种合成式（I）的蒽酰二胺化合物的方法，其中，R1、R2、R3a、R3b、R3c、R4、R5、R6和Z如详细描述中所定义。该方法包括获得式（IV）的单氰基或双氰基取代苯胺化合物的步骤，然后将其转化为式（V）的蒽酰酸化合物或式（Va）的蒽酰胺化合物。此外，式（VI）的化合物可以选择地从式（IV或V或Va）的化合物合成。
• Enantioselective N-Heterocyclic Carbene-Catalyzed Kinetic Resolution of Anilides
  作者：Jianbo Bie、Ming Lang、Jian Wang

  DOI：10.1021/acs.orglett.8b02538

  日期：2018.9.21

  The N-heterocyclic carbene (NHC)-catalyzed enantioselective kinetic resolution of anilides (a kind of hemiaminals) is reported. Upon exposure to the reaction in the presence of an NHC precatalyst and base, catalytic C–O bond formation occurs, providing axially chiral isoindolinones in high yields with excellent enantioselectivities.

  该ñ N-杂环卡宾（NHC）催化苯胺的对映选择性动力学拆分（一种hemiaminals）的报道。在NHC预催化剂和碱的存在下暴露于反应中时，会发生催化C–O键形成，从而以高收率提供轴向手性异吲哚啉酮，并具有出色的对映选择性。
• A convenient and regioselective oxidative bromination of electron-rich aromatic rings using potassium bromide and benzyltriphenylphosphonium peroxymonosulfate under nearly neutral reaction conditions
  作者：Hadi Adibi、Abdol R. Hajipour、Majid Hashemi

  DOI：10.1016/j.tetlet.2006.12.033

  日期：2007.2

  Regioselective oxidative bromination of electron-rich aromatic rings has been studied using potassium bromide as a bromine source in the presence of benzyltriphenylphosphonium peroxymonosulfate as oxidant under nearly neutral reaction conditions. In most cases we obtained monobrominated derivatives regioselectively and in good to high yields without the aid of strong acids.

  在接近中性的反应条件下，在过氧化单硫酸苄基三苯基phosph存在下，使用溴化钾作为溴源，研究了富电子芳环的区域选择性氧化溴化反应。在大多数情况下，我们无需强酸就可以区域选择性地获得高产率的单溴衍生物。
• [EN] PYRROLOPYRIMIDINE AMINES AS COMPLEMENT INHIBITORS<br/>[FR] PYRROLOPYRIMIDINE AMINES EN TANT QU'INHIBITEURS DU COMPLÉMENT
  申请人：BIOCRYST PHARM INC

  公开号：WO2021202977A1

  公开（公告）日：2021-10-07

  Disclosed are compounds of formula (I), and pharmaceutically acceptable salts thereof, which are inhibitors of the complement system. Also provided are pharmaceutical compositions comprising such a compound, and methods of using the compounds and compositions in the treatment or prevention of a disease or condition characterized by aberrant complement system activity.

  本文披露了式（I）的化合物及其药用盐，这些化合物是裂解系统的抑制剂。还提供了包含这种化合物的药物组合物，以及使用这些化合物和组合物治疗或预防由异常裂解系统活动特征的疾病或状况的方法。