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4-ニトロベンジル クロリド

4-Nitrobenzyl chloride

HCID 7482
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
100-14-1
標準SMILES
O=[N+]([O-])c1ccc(CCl)cc1
InChIKey
KGCNHWXDPDPSBV-UHFFFAOYSA-N
分子式
C7H6ClNO2
平均分子量
171.58 g/mol
単同位体質量
171.00870611

概要

Benzene, 1-(chloromethyl)-4-nitro- is a solid. (EPA, 1998)

名称と識別子

優先名称
4-Nitrobenzyl chloride
IUPAC
1-(chloromethyl)-4-nitrobenzene
現地名
4-ニトロベンジル クロリド
英語名
4-Nitrobenzyl chloride
分子式
C7H6ClNO2
分子量
171.58

名称と別名

4-Nitrobenzyl chloride100-14-11-(Chloromethyl)-4-nitrobenzenep-Nitrobenzyl chlorideBenzene, 1-(chloromethyl)-4-nitro-alpha-Chloro-p-nitrotoluenep-(Chloromethyl)nitrobenzene4-(Chloromethyl)nitrobenzeneDTXSID40257454-nitrophenylmethyl chlorideToluene, alpha-chloro-p-nitro-3BLD9LVT3X
名称をさらに表示
4-ニトロベンジル クロリド1-(クロロメチル)-4-ニトロベンゼン4-(クロロメチル)-1-ニトロベンゼン4-ニトロ-1-(クロロメチル)ベンゼン1-ニトロ-4-(クロロメチル)ベンゼンp-ニトロベンジルクロリド4-ニトロベンジルクロリドα-クロロ-p-ニトロトルエン1-クロロメチル-4-ニトロベンゼンα-クロロ-4-ニトロトルエン4-ニトロベンジルクロライド塩化P-ニトロベンジル1‐(クロロメチル)‐4‐ニトロベンゼンΑ‐クロロ‐P‐ニトロトルエン塩化4-ニトロベンジルp-nitrochlorideAKOS BBS-00003951NitrochlorobenzylNitrobenzylchlorideNitrobenzyl chloridà-chloro-4-nitrotolueneα-Chloro-4-nitrotoluene
BENZENE, 1-CHLOROMETHYL-4-NITRO-NSC-9803DTXCID105745CHEBI:87406para-nitrobenzyl chlorideRefChem:525941202-822-7alpha-Chloro-4-nitrotoluene

データベース識別子

CAS
100-14-1
PubChem CID
7482
DTXSID
DTXSID4025745
ChEMBL
CHEMBL176410
ChEBI
CHEBI:87406
UNII
3BLD9LVT3X
EC Number
202-822-7
Nikkaji
J4.978F

物性

構造計算による物性

XLogP
2.5
極性表面積
45.8 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
1
重原子数
11
形式電荷
0
複雑度
138

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Nitros, Aromatic
SpringerMaterials PropertiesDensity
Density1.5647 (NTP, 1992) - Denser than water; will sink
Color/FormPlates or needles from alcohol
Solubility · 2 件

Insoluble (NTP, 1992)

Sol in alcohol, ether, acetone, benzene

Boiling Point230 °C @760 [mm Hg]
Melting Point · 3 件

159.8 °F (EPA, 1998)

71 °C

71 °C

Vapor Pressure0.05 [mm Hg] @25 °C
Refractive IndexIndex of refraction: 1.5647 at 62 °C
Physical Description · 2 件

Benzene, 1-(chloromethyl)-4-nitro- is a solid. (EPA, 1998)

Plates or needles from alcohol; [HSDB]

Other Experimental PropertiesUV: 6794 (Sadtler Research Laboratories Spectral Collection) /Benzyl chloride, 2-nitro/

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information4-Nitrobenzyl chloride: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelCorrosive
Fire HazardsIncompatible with sodium hydroxide. (EPA, 1998)
Health HazardsPoisonous if swallowed or dust is inhaled. (EPA, 1998)
Hazards SummaryPoisonous by ingestion and inhalation; [CAMEO] Corrosive; Causes burns; A lachrymator; May cause pneumonitis and pulmonary edema after inhalation of high concentrations; [MSDSonline]
Reactive GroupHalogenated Organic Compounds
Reactivity Profile · 1 件

Incompatible with sodium hydroxide. [EPA, 1998]. A halogenated aromatic nitro compound. Aromatic nitro compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

化学と産業

薬理情報

Metabolism/Metabolites4-nitrobenzyl chloride has known human metabolites that include 4-nitrobenzyl-glutathione and S-(4-Nitrobenzyl)glutathione.

用途と製造

U.S. Exports(1987) No Data
U.S. Imports(1987) No Data
U.S. Production(1987) No Data
General Manufacturing InformationBenzene, 1-(chloromethyl)-4-nitro-: ACTIVE
応用分野 · 3 件

用途有機合成原料 (NITE総合検索 (ACCESS ON JAN. 2011)

使用4-Nitrobenzyl chloride was used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.

一般的な説明Solid.

調製方法

Chlorination of 4-nitrotoluene at 190 ℃ without catalyst gives 4-Nitrobenzyl chloride. The alternative process of nitration of benzylchloride coproduces 2-nitrobenzyl chloride and requires a difficult separation stage.

純化方法Crystallise the chloride from CCl4, dry diethyl ether, or n-heptane, and dry it under vacuum. IRRITANT.[Beilstein 5 IV 856.]

上流・下流製品情報

下流製品

4-(4-メチルピペラジン-1-イルメチル)フェニルアミン

関連反応

145 件
反応記録を作成
HRID 26402 の反応式
HRID 26402反応物としてuspto-grants-1979_04
HRID 35862 の反応式
HRID 35862反応物としてuspto-grants-1995_05
HRID 37313 の反応式
HRID 37313反応物としてuspto-grants-1995_05
HRID 43057 の反応式
HRID 43057反応物としてuspto-grants-2013_09
HRID 65070 の反応式
HRID 65070反応物としてuspto-grants-1986_09
HRID 83641 の反応式
HRID 83641反応物としてuspto-grants-2014_09
HRID 90151 の反応式
HRID 90151反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 97362 の反応式
HRID 97362反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
1 / 19 ページ

化合物ノート

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物理化学的性質

融点
71 °C · 71 °C
沸点
112 °C · 112 °C (0.6 mmHg)
比重(密度)
1.3246 · 1.3246 (rough estimate)
屈折率
1.5647 · 1.5647 (estimate)
溶解性
50 mg/mL、透明~微かにかすむ、微黄色 · クロロホルム:可溶50mg/mL、透明~微かにかすむ、微黄色
外見
結晶針または粉末
色
ライトイエロー
BRN
387187 · 387187
安定性
安定。 強力な酸化剤、塩基、アミン、湿気、アルコールとは相容れない。 鋼に対して腐食性。 水とゆっくり反応する。 可燃性。
InChI
1S/C7H6ClNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H2
InChIKey
KGCNHWXDPDPSBV-UHFFFAOYSA-N
SMILES
[O-][N+](=O)c1ccc(CCl)cc1
CAS データベース
100 · 100-14-1(CAS DataBase Reference)
NISTの化学物質情報
4 · 4-Nitrobenzyl chloride(100-14-1)
EPAの化学物質情報
1 · 1-(Chloromethyl)-4-nitrobenzene (100-14-1)

化学的性質

化学的特性white to light yellow crystal powde

Air and Water ReactionsMay react slowly with water. (NTP, 1992)
CERCLA Reportable Quantities · 1 件

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzene, 1-(chloromethyl)-4-nitro- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500/10,000 lbs.

Hazard Classes and Categories · 2 件

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

安全と保護具

Fire FightingKeep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.
First Aid · 1 件

Signs and Symptoms of Acute Benzene, 1-(Chloromethyl)-4-Nitro-Exposure: Signs and symptoms of acute exposure to benzene, 1-(chloromethyl)-4-nitro- may be severe and include cyanosis (blue tint to the skin and mucous membranes), tachycardia (rapid heart rate), hypotension (low blood pressure), and cardiac arrhythmias. Respiratory depression and respiratory failure may also occur. Headache, lethargy, weakness, vertigo (dizziness), severe depression, and coma may be noted. GI symptoms include nausea and vomiting. Urine and vomitus may have the odor of bitter almonds.

Nonfire Spill ResponseKeep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. If water pollution occurs, notify appropriate authorities. Do not touch spilled material; stop leak if you can do so without risk.
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 件

0.18 [mg/m3]

2.0 [mg/m3]

12 [mg/m3]

Personal Protective Equipment (PPE) · 1 件

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

毒性情報

Adverse EffectsDermatotoxin - Skin burns.
Non-Human Toxicity Excerpts · 2 件

The mutagenicity of 24 benzyl derivatives, containing a variety of substituents & leaving groups, were assayed in strain TA100 using Ames plate incorporation assay. P-nitrobenzyl chloride (12000 revertants/umole) was mutagenic. It was also mutagenic in strain TA98 (700 revertants/umole), but not in strain TA98NR (a strain deficient in nitro reducatase activity). This study suggests that nitrobenzyl derivatives were mutagenic due to nitro reductive metabolism.

Benzyl chloride, benzyl bromide, p-methylbenzyl chloride, & p-nitrobenzyl chloride were used to study chem reactivity with 4-(p-nitrobenzyl)pyridine & guanosine in vitro, in relation to mutagenic potency in Salmonella typhimurium & sister chromatid exchange (SCE) induction in CHO cells. Benzyl bromide was most reactive, followed by p-methylbenzyl chloride, benzyl chloride, & p-nitrobenzyl chloride. The order of mutagenicity was p-nitrobenzyl chloride much greater than benzyl bromide which was greater than benzyl chloride which was similar or equal to p-methylbenzyl chloride. They caused base-pair mutations only. The order of SCE-inducing ability decreased as follows: benzyl bromide greater than benzyl chloride which was similar or equal to p-nitrobenzyl chloride which was similar or equal to p-methylbenzyl chloride. The high mutagenicity of p-nitrobenzyl chloride in bacteria may be due to reactions other than direct aralkylation.

Toxicity DataLCLo (rat) = 280 mg/m3/4h

法規制情報

CERCLA Reportable Quantities · 1 件

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzene, 1-(chloromethyl)-4-nitro- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500/10,000 lbs.

安全データ

F
4.8-19-21
wgk
3
tsca
TSCA listed
rtecs
XS9093000
ridadr
UN 3261 8/PG 2
hs_code
29049090
risk_code
22-34-36
化審法
(3)-449
消防法
危険物第5類
hazard_code
C
safety_code
26-36/37/39-45-27
hazard_class
8
packing_group
II
Hazard Classifications
Acute Tox. 4 OralSkin Corr. 1B
ストレージクラス
8A - Combustible corrosive hazardous materials
有毒物質データの
100-14-1(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
人的[青]=1
1-メチル-4-(4-ニトロベンジル)ピペラジン
1-(クロロメチル)-2,4-ジニトロベンゼン
1-(4-ニトロベンジル)-1,2,4-トリアゾール
6-(4-ニトロベンジルチオ)-6-デアミノアデノシン
(4-Nitrophenyl)methanesulfonyl chloride
p-Aminobenzylchloride
4-[(ジメチルアミノ)メチル]ベンゼンアミン

補足説明

定義ChEBI: A C-nitro compound that is nitrobenzene in which the hydrogen at position 4 is replaced by a chloromethyl group.