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Cas Database

4276-09-9

4276-09-9

Identification

  • Product Name:1-Butanol,2-amino-3-methyl-, (2R)-

  • CAS Number: 4276-09-9

  • EINECS:217-975-5

  • Molecular Weight:103.164

  • Molecular Formula: C5H13NO

  • HS Code:29051990

  • Mol File:4276-09-9.mol

Synonyms:1-Butanol,2-amino-3-methyl-, (R)-;1-Butanol, 2-amino-3-methyl-, D- (8CI);(-)-2-Amino-3-methyl-1-butanol;(-)-Valinol;(2R)-2-Amino-3-methylbutan-1-ol;(R)-2-Amino-3-methyl-1-butanol;(R)-2-Amino-3-methylbutanol;(R)-Valinol;D-Valinol;[(R)-1-(Hydroxymethyl)-2-methylpropyl]amine;D-Val-ol;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
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  • Price
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  • Manufacture/Brand:Usbiological
  • Product Description:D-Valinol
  • Packaging:1g
  • Price:$ 156
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:D-Valinol
  • Packaging:5g
  • Price:$ 80
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:D-Valinol >98.0%(GC)(T)
  • Packaging:5g
  • Price:$ 116
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:D-Valinol >98.0%(GC)(T)
  • Packaging:1g
  • Price:$ 40
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:(R)-(-)-2-Amino-3-methylbutan-1-ol
  • Packaging:25 g
  • Price:$ 77
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(R)-(?)-2-Amino-3-methyl-1-butanol 98%
  • Packaging:5g
  • Price:$ 178
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(R)-(?)-2-Amino-3-methyl-1-butanol 98%
  • Packaging:1g
  • Price:$ 68.6
  • Delivery:In stock
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  • Manufacture/Brand:Oakwood
  • Product Description:D-Valinol 98%
  • Packaging:5g
  • Price:$ 14
  • Delivery:In stock
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:D-Valinol
  • Packaging:5 mg
  • Price:$ 790
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:D-Valinol
  • Packaging:50 mg
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Relevant articles and documentsAll total 29 Articles be found

A Spiroalkylation Method for the Stereoselective Construction of α-Quaternary Carbons and Its Application to the Total Synthesis of (R)-Puraquinonic Acid

Elmehriki, Adam A. H.,Gleason, James L.

supporting information, p. 9729 - 9733 (2019/12/02)

Cyclic α-quaternary carbon stereocenters were prepared from biselectrophillic substrates and an easily prepared chiral bicyclic sulfonyl lactam. This was achieved in two steps by spiroalkylation, employing biphasic reaction conditions with a phase-transfer catalyst, followed by reduction and alkylation with a series of alkyl halide electrophiles. The products of this method were isolated in good yields with with high levels of diastereoselectivity. This methodology was employed in the enantioselective total synthesis of (R)-puraquinonic acid (1) for a late-stage installation of the α-quaternary carbon stereocenter. This enabled the shortest synthesis of 1 to date, an eight-pot sequence providing an overall yield of 14%.

Total Enantioselective Synthesis of the Endophytic Fungal Polyketide Phomolide H and Its Structural Revision

McNulty, James,McLeod, David

supporting information, p. 29 - 33 (2017/01/14)

A total synthesis of the proposed structure of the natural polyketide-macrolactone phomolide H 2 has been achieved following a bidirectional strategy from l-tartaric acid. The originally assigned structure of phomolide H displayed discordant NMR spectroscopic data in comparison with synthetic 2. The synthetic strategy was extended to prepare diastereomers and epimeric methyl-ethers of the natural product, structural analysis of which revealed a match of the natural product with diastereomer 27. The structural revision of phomolide H from 2 to the methanol solvate of compound 27 is presented.

Heterogeneous Catalytic Hydrogenation of Chiral Amino Acid Methyl Esters to Amino Alcohols with Retention of Configuration Over Mg-Modified Cu/ZnO/Al2O3 Catalyst

Zhan, Bing,Zhang, Shuangshuang,Yu, Jun,Xiao, Xiuzheng,Guo, Xiaoming,Mao, Dongsen,Lu, Guanzhong

, p. 2160 - 2166 (2017/07/25)

Selective hydrogenation of amino acid methyl esters to chiral amino alcohols is an important and fascinating process. The CuZn0.3Mg0.1AlOx catalyst for the synthesis of chiral amino alcohols was prepared by the fractional

Enantioselective Total Synthesis of the Proposed Structure of the Endophytic Fungal Metabolite Phomolide G: Structural Revision and Unambiguous Stereochemical Assignment

McNulty, James,McLeod, David,Jenkins, Hilary A.

supporting information, p. 688 - 692 (2017/01/18)

A total synthesis of the proposed structure of the natural macrolactone phomolide G (1) by a bidirectional strategy from L-tartaric acid is reported. The ω-terminus of the molecule was elaborated by nitrile extension, C3-alkylation and a substrate-controlled 1,3-ketone reduction. The α-terminus was extended by a C2aldehyde-to-alkenal homologation followed by an auxiliary controlled aldol reaction. Macrolactonization and deprotection yielded compound 1 (confirmed by X-ray analysis). This putative structure of phomolide G displayed discordant NMR spectroscopic data in comparison with those of the natural product. Detailed inspection of all NMR spectroscopic data available indicated phomolide G to be likely a diastereomer of 1. The synthetic strategy developed allows control of the absolute stereochemistry at all four chiral secondary alcohol groups. Further manipulation allowed for the preparation of diastereomer 33, the1H and13C NMR spectroscopic data of which are in full accord with that reported for the natural product.

Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

Li, Shengkun,Li, Dangdang,Xiao, Taifeng,Zhang, Shasha,Song, Zehua,Ma, Hongyu

, p. 8927 - 8934 (2016/12/07)

Chirality greatly influences the biological and pharmacological properties of a pesticide and will contribute to unnecessary environmental loading and undesired ecological impact. No structure and activity relationship (SAR) of enantiopure succinate dehydrogenase inhibitors (SDHIs) was documented during the structure optimization of boscalids. On the basis of commercial SDHIs, oxazoline natural products, and versatile oxazoline ligands in organic synthesis, the first effort was devoted to explore the chiral SDHIs and the preliminary mechanism thereof. Fine-tuning furnished chiral nicotinamides 4ag as a more promising fungicidal candidate against Rhizoctonia solani, Botrytis cinerea, and Sclerotinia sclerotiorum, with EC50 values of 0.58, 0.42, and 2.10 mg/L, respectively. In vivo bioassay and molecular docking were investigated to explore the potential in practical application and plausible novelty in action mechanism, respectively. The unexpected molecular docking model showed the different chiral effects on the binding site with the amino acid residues. This chiral nicotinamide also featured easy synthesis and cost-efficacy. It will provide a powerful complement to the commercial SDHI fungicides with the introduction of chirality.

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
With lithium borohydride; chloro-trimethyl-silane; In tetrahydrofuran; at 20 ℃; for 0.25h;
92%
With sodium tetrahydroborate; iodine; In tetrahydrofuran; Inert atmosphere;
91%
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 17h; Reflux;
74%
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 17h; Reflux; Inert atmosphere;
74%
With lithium aluminium tetrahydride; In tetrahydrofuran;
With sodium tetrahydroborate; iodine; In tetrahydrofuran; Heating;
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / 40 °C
2: sodium borohydride / ethanol; H2O / 5.5 h / Heating
With sodium tetrahydroborate; thionyl chloride; In ethanol; water;
With lithium aluminium tetrahydride; In tetrahydrofuran; for 16h; Heating;
With lithium aluminium tetrahydride;
With sodium tetrahydroborate; iodine;
With sodium tetrahydroborate; iodine; In tetrahydrofuran;
With borane-THF; In tetrahydrofuran; at 20 ℃; for 17h; Reflux;
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 - 64 ℃; Inert atmosphere;
With lithium aluminium tetrahydride; In tetrahydrofuran;
With sodium tetrahydroborate; iodine; In tetrahydrofuran; Inert atmosphere; Schlenk technique;
With sodium tetrahydroborate; iodine; In tetrahydrofuran; Inert atmosphere; Schlenk technique;
With sodium tetrahydroborate; iodine;
With sodium tetrahydroborate; iodine; In tetrahydrofuran; for 18h; Reflux;
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere
1.2: 24 h / 0 °C / Inert atmosphere; Reflux
2.1: potassium hydroxide / water / 4 h / Inert atmosphere
With sodium tetrahydroborate; potassium hydroxide; In tetrahydrofuran; water;
With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 80 ℃; for 12h; Inert atmosphere; Schlenk technique;
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 ℃; Inert atmosphere; Reflux;
D-Valine methyl ester hydrochloride
7146-15-8

D-Valine methyl ester hydrochloride

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
D-Valine methyl ester hydrochloride; With sodium carbonate; In water; pH=8;
With CuZn0.3Mg0.1AlO(x); hydrogen; In ethanol; at 80 ℃; for 10h; under 37503.8 Torr; Autoclave;
57.4 %Chromat.
(R)-2-amino-3-methylbutyronitrile hydrochloride

(R)-2-amino-3-methylbutyronitrile hydrochloride

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

3-methyl-butane-1,2-diamine

3-methyl-butane-1,2-diamine

Conditions
Conditions Yield
With hydrogenchloride; methanol; water; hydrogen; palladium over charcoal; for 28h; under 7500.75 - 37503.8 Torr;
dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

3,3-dimethylpent-4-enoic acid chloride
88819-78-7

3,3-dimethylpent-4-enoic acid chloride

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
With NaH; Fe(CO)5; In tetrahydrofuran; tetrachloromethane;
(1R,1'R)-N-benzyl-1-phenyl-1'-isopropyl-2,2'-dihydroxydiethylamine

(1R,1'R)-N-benzyl-1-phenyl-1'-isopropyl-2,2'-dihydroxydiethylamine

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
With ammonium formate; palladium on activated charcoal; In methanol; for 2h; Heating;
53%
(R)-(-)-valine ethyl ester
3350-55-8,13893-45-3,17431-03-7

(R)-(-)-valine ethyl ester

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In diethyl ether;
(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
D-Valine methyl ester hydrochloride
7146-15-8

D-Valine methyl ester hydrochloride

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
With sodium tetrahydroborate; In ethanol; water; for 5.5h; Heating;
D-valine
1293368-27-0

D-valine

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
With potassium hydroxide; In water; for 4h; Inert atmosphere;
D-Valine methyl ester
4070-48-8,18869-42-6,21685-47-2

D-Valine methyl ester

(R)-2-amino-3-methylbutanol
4276-09-9,473-75-6

(R)-2-amino-3-methylbutanol

Conditions
Conditions Yield
With sodium tetrahydroborate;
15%

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