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4-CHROMANOL, also known as 4-Hydroxychroman, is a white crystalline low melting solid with unique chemical properties. It is a naturally occurring compound found in various plants and has been identified for its potential applications in different industries due to its distinctive characteristics.

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  • 1481-93-2 Structure
  • Basic information

    1. Product Name: 4-CHROMANOL
    2. Synonyms: 4-HYDROXYCHROMAN;4-CHROMANOL;3,4-DIHYDRO-2H-1-BENZOPYRAN-4-OL;2H-1-Benzopyran-4-ol, 3,4-dihydro-;Chroman-4-ol;Chromanol;4-CHROMANOL, 99+%;4-CHROMANOL 96%
    3. CAS NO:1481-93-2
    4. Molecular Formula: C9H10O2
    5. Molecular Weight: 150.17
    6. EINECS: 216-041-4
    7. Product Categories: N/A
    8. Mol File: 1481-93-2.mol
  • Chemical Properties

    1. Melting Point: 42-44 °C(lit.)
    2. Boiling Point: 80 °C (5 mmHg)
    3. Flash Point: >230 °F
    4. Appearance: white crystalline low melting solid
    5. Density: 0.9820 (rough estimate)
    6. Vapor Pressure: 0.00425mmHg at 25°C
    7. Refractive Index: 1.5470 (estimate)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 14.12±0.20(Predicted)
    11. BRN: 130800
    12. CAS DataBase Reference: 4-CHROMANOL(CAS DataBase Reference)
    13. NIST Chemistry Reference: 4-CHROMANOL(1481-93-2)
    14. EPA Substance Registry System: 4-CHROMANOL(1481-93-2)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 24/25-36-26
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1481-93-2(Hazardous Substances Data)

1481-93-2 Usage

Uses

Used in Pharmaceutical Industry:
4-CHROMANOL is used as a key intermediate for the synthesis of various pharmaceutical compounds, particularly for the preparation of 4-α-L-rhamnopyranosyloxychromanol, a glycosyl flavonoid. This flavonoid is known for its potential therapeutic properties, including antioxidant and anti-inflammatory activities, which can be beneficial in the development of new drugs for various health conditions.
Used in Chemical Synthesis:
4-CHROMANOL is used as a versatile building block in the synthesis of a wide range of organic compounds, including natural products, pharmaceuticals, and agrochemicals. Its unique chemical properties make it a valuable starting material for the development of new molecules with potential applications in various industries.
Used in Research and Development:
4-CHROMANOL is utilized as a research compound in the field of organic chemistry, where it serves as a model for studying the structure, properties, and reactivity of chromanol-based compounds. This knowledge can be applied to the design and synthesis of new molecules with specific functions and applications.

Check Digit Verification of cas no

The CAS Registry Mumber 1481-93-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,8 and 1 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1481-93:
(6*1)+(5*4)+(4*8)+(3*1)+(2*9)+(1*3)=82
82 % 10 = 2
So 1481-93-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-4,8,10H,5-6H2/t8-/m0/s1

1481-93-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Alfa Aesar

  • (A14940)  4-Chromanol, 97%   

  • 1481-93-2

  • 1g

  • 397.0CNY

  • Detail
  • Alfa Aesar

  • (A14940)  4-Chromanol, 97%   

  • 1481-93-2

  • 5g

  • 1014.0CNY

  • Detail
  • Alfa Aesar

  • (A14940)  4-Chromanol, 97%   

  • 1481-93-2

  • 25g

  • 2375.0CNY

  • Detail
  • Aldrich

  • (303895)  4-Chromanol  ≥99%

  • 1481-93-2

  • 303895-1G

  • 490.23CNY

  • Detail

1481-93-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Chromanol

1.2 Other means of identification

Product number -
Other names 4-Hydroxychroman

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:1481-93-2 SDS

1481-93-2Relevant articles and documents

Enantioselective reduction of prochiral ketones by chromium(II) complexes with amino acid ligands as the source of chirality

Patonay,Hajdu,Jeko,Levai,Micskei,Zucchi

, p. 1373 - 1374 (1999)

Prochiral ketones were reduced to enantiomerically enriched secondary alcohols by Cr(II)[L-amino acid] complexes in good yields and moderate enantioselectivity.

Copper-Catalyzed Asymmetric Hydroboration of 2 H-Chromenes Using a Chiral Diphosphine Ligand

Li, Xiufen,Wang, Chaoqiong,Song, Jianqiao,Yang, Zhihong,Zi, Guofu,Hou, Guohua

, p. 8638 - 8645 (2019)

A highly regioselective asymmetric hydroboration of 2H-chromenes catalyzed by the complex of CuCl and diphosphine ligand (S,R)-DuanPhos has been realized under mild conditions to produce 3-boryl chromans, achieving good yields and excellent enantioselectivities up to 96% ee. This work provides an efficient approach to the synthesis of chiral 3-boryl chromans and derivatives.

Half-sandwich Ru (II) complexes containing (N, O) Schiff base ligands: Catalysts for base-free transfer hydrogenation of ketones

Satheesh,Sathish Kumar, Pushpanathan N.,Kumara, P. Raghavendra,Karvembu, Ramasamy,Hosamani, Amar,Nethaji

, (2019)

Two new half-sandwich Ru (II)(p-cymene) complexes (1 and 2) containing dopamine-based (N, O) Schiff base ligands (L1H and L2H) were synthesized and characterized by FT-IR, UV–Visible and 1H & 13C NMR spectral techniques, and elemental analyses. The spectroscopic and analytical data revealed monobasic bidentate coordination of the ligands with Ru ion. The molecular structures of L1H, L2H and 2 were further confirmed by single crystal X-ray diffraction study. Complexes 1 and 2?have been employed as catalysts in the transfer hydrogenation of ketones using 2-propanol as a hydrogen source at 85?°C under base-free condition. Good to the excellent yield of secondary alcohols, gram scale synthesis, and high TON and TOF made this catalytic system interesting.

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

Oestreich, Martin,Seliger, Jan

supporting information, p. 247 - 251 (2020/10/29)

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.

Chitosan as a chiral ligand and organocatalyst: Preparation conditions-property-catalytic performance relationships

Kolcsár, Vanessza Judit,Sz?ll?si, Gy?rgy

, p. 7652 - 7666 (2021/12/13)

Chitosan is an abundant and renewable chirality source of natural origin. The effect of the preparation conditions by alkaline hydrolysis of chitin on the properties of chitosan was studied. The materials obtained were used as ligands in the ruthenium-catalysed asymmetric transfer hydrogenation of aromatic prochiral ketones and oxidative kinetic resolution of benzylic alcohols as well as organocatalysts in the Michael addition of isobutyraldehyde to N-substituted maleimides. The degrees of deacetylation of the prepared materials were determined by 1H NMR, FT-IR and UV-vis spectroscopy, the molecular weights by viscosity measurements, their crystallinity by WAXRD, and their morphology by SEM and TEM investigations. The materials were also characterized by Raman spectroscopy. The biopolymers which have molecular weights in a narrow (200-230 kDa) range and appropriate (80-95%) degrees of deacetylation were the most efficient ligands in the enantioselective transfer hydrogenation, whereas in the oxidative kinetic resolution the activity of the complexes and the stereoselectivity increased with the degree of deacetylation. The chirality of the chitosan was sufficient to obtain enantioselection in the Michael addition of isobutyraldehyde to maleimides in the aqueous phase. Interestingly, the biopolymer afforded the opposite enantiomer in excess compared to the monomer, d-glucosamine. In this reaction, good correlation between the degree of deacetylation and the catalytic activity was found. These results are novel steps in the application of this natural, biocompatible and biodegradable polymer in developing environmentally benign methods for the production of optically pure fine chemicals.

Palladium Complexes Bearing Chiral bis(NHC) Chelating Ligands on a Spiro Scaffold: Synthesis, Characterization, and Their Application in the Oxidative Kinetic Resolution of Secondary Alcohols

Zhang, Dao,Yu, Jueqin

, p. 605 - 613 (2020/02/13)

A series of chiral bis-N-heterocyclic carbene ligands H2[(S)-1a-d]X2 (X = Br, I) on a spiro scaffold and their palladium complexes (S)-2a-d and (S)-3a,b were prepared and applied in the enantioselective oxidative kinetic resolution of secondary alcohols. The corresponding alcohols can be obtained in high yields with moderate to excellent ee values.

Diboron-Mediated Rhodium-Catalysed Transfer Hydrogenation of Alkenes and Carbonyls

Lin, Xiao,Wang, Yuhan,Hu, Yan,Zhu, Wanjiang,Dou, Xiaowei

supporting information, p. 1046 - 1049 (2020/02/25)

A diboron-mediated rhodium-catalysed transfer hydrogenation system using water as the hydrogen donor is developed. In addition to a series of alkenes with good functional group tolerance, this rhodium-based catalytic system also effectively reduces aldehydes and ketones. A plausible mechanism involving the RhI-catalysed hydrogen generation and Rh0-catalysed hydrogenation is proposed for the reaction.

Enantioselective Synthesis of 4-Cyanotetrahydroquinolines via Ni-Catalyzed Hydrocyanation of 1,2-Dihydroquinolines

Fang, Xianjie,Gao, Jihui,Jiao, Mingdong

supporting information, (2020/11/18)

A Ni-catalyzed asymmetric hydrocyanation that enables the formation of 4-cyanotetrahydroquinolines in good yields with excellent enantioselectivities is presented herein. A variety of functional groups are well-tolerated, and a gram-scale reaction supports the synthetic potential of the transformation. Additionally, several crucial intermediates for pharmaceutically active agents, including a PGD2 receptor antagonist, are now accessible through asymmetric synthesis using this new protocol.

Highly Enantioselective Transfer Hydrogenation of Prochiral Ketones Using Ru(II)-Chitosan Catalyst in Aqueous Media

Sz?ll?si, Gy?rgy,Kolcsár, Vanessza Judit

, p. 820 - 830 (2018/12/13)

Unprecedentedly high enantioselectivities are obtained in the transfer hydrogenation of prochiral ketones catalyzed by a Ru complex formed in situ with chitosan chiral ligand. This biocompatible, biodegradable chiral polymer obtained from the natural chitin afforded good, up to 86 % enantioselectivities, in the aqueous-phase transfer hydrogenation of acetophenone derivatives using HCOONa as hydrogen donor. Cyclic ketones were transformed in even higher, over 90 %, enantioselectivities, whereas further increase, up to 97 %, was obtained in the transfer hydrogenations of heterocyclic ketones. The chiral catalyst precursor prepared ex situ was examined by scanning electron microscopy, FT-mid- and -far-IR spectroscopy. The structure of the in situ formed catalyst was investigated by 1H NMR spectroscopy and using various chitosan derivatives. It was shown that a Ru pre-catalyst is formed by coordination of the biopolymer to the metal by amino groups. This precursor is transformed in water insoluble Ru-hydride complex following hydrogen donor addition. The practical value of the developed method was verified by preparing over twenty chiral alcohols in good yields and optical purities. The catalyst was applied for obtaining optically pure chiral alcohols at gram scale following a single crystallization.

Ruthenium(II)-Chitosan, an Enantioselective Catalyst for the Transfer Hydrogenation of N-Heterocyclic Ketones

Kolcsár, Vanessza Judit,Fül?p, Ferenc,Sz?ll?si, Gy?rgy

, p. 2725 - 2731 (2019/05/24)

The present study aimed at extending the applicability of a recently developed stereoselective catalytic system to the preparation of optically enriched N-heterocyclic alcohols. Chiral ruthenium catalyst formed in situ using the chitosan biopolymer as ligand, which provided good results in the transfer hydrogenation of heterobicyclic compounds, such as 4-chromanone and 4-thiochromanone, was used in reactions of various N-containing prochiral ketones. High enantioselectivities were reached in transfer hydrogenations of bicyclic compounds bearing nitrogen either in aromatic or cycloaliphatic moieties, provided that the amino group was protected or shielded by a nearby substituent. Results were rationalized by interactions of the nitrogen with the metal and/or ligand. N-containing bicyclic compounds having heteroatoms in both rings were also prepared and tested. The detrimental effect of the pyridyl moiety was compensated by the beneficial influence of the heteroatom in the cycloaliphatic ring, as indicated by high rates and good enantioselectivities obtained in reactions of these compounds. Preparation of several N-heterocyclic alcohols, in good yields and high optical purities was achieved using Ru(II)-chitosan complex.

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