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(1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL is a chiral chemical compound with the molecular formula C10H13BrO. It features a tetrahydro-naphthalene ring with a bromine atom and a hydroxyl group attached, giving it unique chemical properties and potential applications across various fields.

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  • 39834-40-7 Structure
  • Basic information

    1. Product Name: (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL
    2. Synonyms: (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL;Trans-2-Bromo-1-TeTralol
    3. CAS NO:39834-40-7
    4. Molecular Formula: C10H11BrO
    5. Molecular Weight: 227.09774
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 39834-40-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 337°C at 760 mmHg
    3. Flash Point: 157.6°C
    4. Appearance: /
    5. Density: 1.538g/cm3
    6. Vapor Pressure: 4.23E-05mmHg at 25°C
    7. Refractive Index: 1.628
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL(CAS DataBase Reference)
    11. NIST Chemistry Reference: (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL(39834-40-7)
    12. EPA Substance Registry System: (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL(39834-40-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 39834-40-7(Hazardous Substances Data)

39834-40-7 Usage

Uses

Used in Organic Synthesis:
(1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL is used as a building block in organic synthesis for the preparation of various biologically active compounds. Its unique structure allows for the creation of a wide range of molecules with potential applications in different industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL is utilized as a precursor for the synthesis of pharmaceuticals. Its chiral nature and functional groups make it a valuable component in the development of new drugs with specific therapeutic effects.
Used in Agrochemicals:
(1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL may also serve as a precursor in the synthesis of agrochemicals, contributing to the development of effective pesticides, herbicides, and other agricultural products.
Used in Fragrance and Flavoring Industry:
Due to its aromatic nature, (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL has potential applications in the fragrance and flavoring industry. It can be used to create unique scents and flavors for various consumer products, such as perfumes, candles, and food items.

Check Digit Verification of cas no

The CAS Registry Mumber 39834-40-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,8,3 and 4 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 39834-40:
(7*3)+(6*9)+(5*8)+(4*3)+(3*4)+(2*4)+(1*0)=147
147 % 10 = 7
So 39834-40-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H11BrO/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-4,9-10,12H,5-6H2/t9-,10+/m1/s1

39834-40-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (1S,2R)-2-BROMO-1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-OL

1.2 Other means of identification

Product number -
Other names trans-2-bromo-1,2,3,4-tetrahydro-1-naphthol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:39834-40-7 SDS

39834-40-7Relevant articles and documents

Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides

Lee, Jeong Min,Bae, Dae Young,Park, Jin Yong,Jo, Hwi Yul,Lee, Eunsung,Rhee, Young Ho,Park, Jaiwook

supporting information, p. 4608 - 4613 (2020/06/05)

A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.

Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins

Ai, Lingsheng,Wang, Weijin,Wei, Jialiang,Li, Qing,Song, Song,Jiao, Ning

supporting information, p. 437 - 441 (2019/02/26)

β-Halohydrins bearing transformable halo- and hydroxyl groups, are easily converted into various valuable blocks in organic and pharmaceutical synthesis. A diastereoselective β-halogenation of benzylic alcohols was achieved under simple and low-cost conditions, which provided a direct synthesis of β-halohydrins. The simple reaction conditions, easily available reagents, high diastereoselectivities, and additional oxidant-free make this reaction very attractive and practical.

Bromination of olefins with HBr and DMSO

Karki, Megha,Magolan, Jakob

, p. 3701 - 3707 (2015/04/22)

A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.

From simple organobromides or olefins to highly value-added bromohydrins: A versatile performance of dimethyl sulfoxide

Song, Song,Huang, Xiaoqiang,Liang, Yu-Feng,Tang, Conghui,Li, Xinwei,Jiao, Ning

supporting information, p. 2727 - 2731 (2015/05/27)

A novel and efficient direct transformation of secondary bromides or olefins to highly value-added bromohydrins has been disclosed. Dimethyl sulfoxide (DMSO), a cheap and common solvent, performs its versatile role as a solvent, an essential oxidant, and also as an oxygen source in this bromohydrin synthesis.

Discovery of a novel class of dimeric smac mimetics as potent IAP antagonists resulting in a clinical candidate for the treatment of cancer (AZD5582)

Hennessy, Edward J.,Adam, Ammar,Aquila, Brian M.,Castriotta, Lillian M.,Cook, Donald,Hattersley, Maureen,Hird, Alexander W.,Huntington, Christopher,Kamhi, Victor M.,Laing, Naomi M.,Li, Danyang,MacIntyre, Terry,Omer, Charles A.,Oza, Vibha,Patterson, Troy,Repik, Galina,Rooney, Michael T.,Saeh, Jamal C.,Sha, Li,Vasbinder, Melissa M.,Wang, Haiyun,Whitston, David

, p. 9897 - 9919 (2014/01/17)

A series of dimeric compounds based on the AVPI motif of Smac were designed and prepared as antagonists of the inhibitor of apoptosis proteins (IAPs). Optimization of cellular potency, physical properties, and pharmacokinetic parameters led to the identification of compound 14 (AZD5582), which binds potently to the BIR3 domains of cIAP1, cIAP2, and XIAP (IC50 = 15, 21, and 15 nM, respectively). This compound causes cIAP1 degradation and induces apoptosis in the MDA-MB-231 breast cancer cell line at subnanomolar concentrations in vitro. When administered intravenously to MDA-MB-231 xenograft-bearing mice, 14 results in cIAP1 degradation and caspase-3 cleavage within tumor cells and causes substantial tumor regressions following two weekly doses of 3.0 mg/kg. Antiproliferative effects are observed with 14 in only a small subset of the over 200 cancer cell lines examined, consistent with other published IAP inhibitors. As a result of its in vitro and in vivo profile, 14 was nominated as a candidate for clinical development.

Highly regio- and diastereoselective halohydroxylation of olefins: A facile synthesis of vicinal halohydrins

Zhang, Jinglei,Wang, Jie,Qiu, Zhuibai,Wang, Yang

experimental part, p. 6859 - 6867 (2011/10/02)

An efficient method for the synthesis of vicinal chlorohydrin or bromohydrin derivatives has been developed on the basis of direct halohydroxylation of various olefins with electrondonating or withdrawing substituent. The reactions were carried out under mild conditions in the presence of N-tosyl-l-threonine (NTsLT) as an acidic additive using chloramine T trihydrate, 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) or N-bromoacetamide (AcNHBr) as the halogen source, respectively, affording the corresponding vicinal halohydrins in good to high yields with excellent regio- and stereoselectivities.

Asymmetric synthesis of chiral 1,3-diaminopropanols: Bisoxazolidine- catalyzed C-C bond formation with α-keto amides

Xu, Hanhui,Wolf, Christian

, p. 12249 - 12252 (2012/02/01)

Three high-yielding steps lead to the formation of chiral 1,3-diaminopropanols from aliphatic and aromatic α-keto amides. In this approach, a nitroaldol reaction, which is catalyzed by Cu(SO2CF 3)2 and the bisoxazolidine ligand L1, is followed by two mild reduction reactions (see scheme). Laborious protection and deprotection steps can be avoided by using this method.

Organocatalysis in the stereoselective bromohydrin reaction of alkenes

Bar, Sukanta

experimental part, p. 605 - 612 (2010/08/21)

An efficient regio- and stereo-selective (>99:1) trans-bromohydrination (bromohydroxylation and bromomethoxylation) of alkenes including α,β-unsaturated carbonyl compounds with N-bromosuccinimide (NBS) has been achieved by using 1.0 mol% of N,N'-diarylthi

Et2Zn-mediated rearrangement of bromohydrins

Li, Lezhen,Cai, Peijie,Guo, Qingxiang,Xue, Song

, p. 3516 - 3522 (2008/09/20)

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Piperazine compounds

-

Page/Page column 10-11, (2008/06/13)

A compound selected from those of formula (I): wherein: R1, R2, R3 and R4, which may be the same or different, each represent an atom or group selected from hydrogen, halogen, alkyl, alkoxy, phenyl and cyano, X represents a bond, an oxygen atom or a group selected from —(CH2)m—, —OCH2— and —NR5—, wherein m represents 1 or 2, and R5 is as defined in the description, Y represents an oxygen atom or a group selected from NR7 and CHR8, wherein R7 and R8 are as defined in the description, Z represents a nitrogen atom or a CH group, n represents 1 or 2, Ak represents an alkylene chain, Ar represents an aryl or heteroaryl group, its optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medical products containing the same which are useful in the treatment of conditions requiring a serotonin reuptake inhibitor and/or NK1 antagonist.

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